2-Methyltetrahydrofuran and cyclopentyl methyl ether for green solid-phase peptide synthesis

Jad, Yahya E.; Acosta, Gerardo; Khattab, Sherine N.; Torre, Beatriz G. de la; Govender, Thavendran; Kruger, Hendrik G.; El‐Faham, Ayman; Alberício, Fernando

doi:10.1007/s00726-015-2095-x

Cited by 76 publications

(102 citation statements)

References 32 publications

Supporting

Mentioning

102

Contrasting

Order By: Relevance

“…These solvents despite not being considered green solvents, constitute an environmentally friendlier approach than DMF and CH 2 Cl 2 . Later, the lab expanded McMillan's methodology by using 2‐MeTHF and CPME as greener alternatives to THF and MeCN for amide bond formation in peptide synthesis . Their results showed that resin swelling was not compromised in either solvent.…”

Section: Attempts To Make a Greener Protocolmentioning

confidence: 99%

See 1 more Smart Citation

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Varnava

Sarojini

2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

To date, the synthesis of peptides is concurrent with the production of enormous amounts of toxic waste. DMF, CH2Cl2, and NMP are three of the most toxic organic solvents used in chemical synthesis and are the most common solvents used for peptide synthesis. Additionally, concerns about the hepatotoxicity caused by exposure to DMF and from the toxic and allergenic nature of additives used in peptide synthesis necessitates the need for a green, environmentally friendly, and safer protocol for peptide synthesis. This review summarizes the current literature on green solid‐phase peptide synthesis successes and challenges encountered. The review concludes with suggestions for future research towards a simple and efficient green peptide synthesis protocol.

show abstract

Section: Attempts To Make a Greener Protocolmentioning

confidence: 99%

“…However, several Fmoc‐amino acids were not soluble in CPME. Additionally, Fmoc removal by using 20 % piperidine in these solvents was not successful . This obstacle was recently resolved when the authors screened different piperidine cocktails by using a range of solvents in both ChemMatrix and PS resins .…”

Section: Attempts To Make a Greener Protocolmentioning

confidence: 99%

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Varnava

Sarojini

2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…Acosta et al then demonstrated the suitability of acetonitrile for SPPS in the preparation of the test peptides Leu-enkephalinamide and acyl carrier protein (ACP 65-74) (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-NH 2 ), upon PEG-based resins in excellent crude purity [30]. Subsequent reports from Albericio and co-workers have continued along the same theme of using less problematic alternatives to DMF for SPPS couplings, with the use of acetonitrile explored in more detail, along with THF, 2-MeTHF and CPME [32,33]. Importantly, the solution-phase synthesis of Z-Phg-Pro-NH 2 indicated each of these solvents performed as well, if not better, than DMF, in suppressing racemisation.…”

Section: Alternative Organic Solventsmentioning

confidence: 99%

“…2-MeTHF and CPME performed much worse on PEG-resins using the aforementioned test sequence. They were however, found to suitably swell PS-resins and excellent results were obtained for 2-MeTHF, with only 3.0 % of the des-Aib sequence observed [33].…”

Section: Alternative Organic Solventsmentioning

confidence: 99%

Greener solvents for solid-phase organic synthesis

Lawrenson

2017

Pure and Applied Chemistry

View full text Add to dashboard Cite

Solid-phase organic synthesis is an essential method for the rapid synthesis of complex biological structures and libraries of small organic molecules. However, it is often associated with the use of large quantities of problematic solvents for the removal of excess reagents and reaction by-products. Given that solvent will often be the biggest contributor to waste generated in the average pharmaceutical/fine-chemical process, its exchange for a more desirable alternative often presents the biggest gains in terms of reducing environmental impact. This review aims to explore recent approaches to performing solid-phase organic synthesis, and associated solid-phase peptide synthesis, in neoteric solvents and reaction media that present greener alternatives.

show abstract

“…CPME is an ethereal solvent that has gained interest as a suitable industrial solvent with improved characteristics compared to other ethereal solvents including: better stability to peroxide formation, low volatility, low water solubility, and acidic stability . Furthermore, according to Sakamoto, CPME synthesis is 100% atom efficient, produced by the addition of methanol to cyclopentene, and has been demonstrated in many applications including furfural synthesis, secondary thioamide synthesis, carotenoid extraction, peptide synthesis, protein purification, and radical additions . CPME exposure was not found to cause genotoxity or mutagenicity but further assessment is needed to determine its toxicological profile …”

Section: Introductionmentioning

confidence: 99%

Evaluation of green solvents: Oil extraction from oleaginous yeast Lipomyces starkeyi using cyclopentyl methyl ether (CPME)

Probst

Wales

Rezac

et al. 2017

Biotechnology Progress

View full text Add to dashboard Cite

Cyclopentyl methyl ether (CPME) was evaluated for extracting oil or triacylglycerol (TAG) from wet cells of the oleaginous yeast Lipomyces starkeyi. CPME is a greener alternative to chloroform as a potential solvent for oil recovery. A monophasic system of CPME and biphasic system of CPME:water (1:0.7) performed poorly having the lowest TAG extraction efficiency and TAG selectivity compared to other monophasic systems of hexane and chloroform and the biphasic Bligh and Dyer method (chloroform:methanol:water). Biphasic systems of CPME:water:alcohol (methanol/ethanol/1-propanol) were tested and methanol achieved the best oil extraction efficiency compared to ethanol and 1-propanol. Different biphasic systems of CPME:methanol:water were tested, the best TAG extraction efficiency and TAG selectivity achieved was 9.9 mg/mL and 64.6%, respectively, using a starting ratio of 1:1.7:0.6 and a final ratio of 1:1:0.8 (CPME:methanol:water). Similar results were achieved for the Bligh and Dyer method (TAG extraction efficiency of 10.2 mg/mL and TAG selectivity of 66.0%) indicating that the biphasic CPME system was comparable. The fatty acid profile remained constant across all the solvent systems tested indicating that choice of solvent was not specific for any certain fatty acid. This study was able to demonstrate that CPME could be used as an alternative solvent for the extraction of oil from the wet biomass of oleaginous yeast. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 33:1096-1103, 2017.

show abstract

2-Methyltetrahydrofuran and cyclopentyl methyl ether for green solid-phase peptide synthesis

Cited by 76 publications

References 32 publications

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Making Solid‐Phase Peptide Synthesis Greener: A Review of the Literature

Greener solvents for solid-phase organic synthesis

Evaluation of green solvents: Oil extraction from oleaginous yeast Lipomyces starkeyi using cyclopentyl methyl ether (CPME)

Contact Info

Product

Resources

About